Reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)([Cl:20])=O>>[Cl:20][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[CH:13]1Participants
Conditions
- Temperature
- 80 °C
Procedure
A round bottom flask was charged with a magnetic stir bar, 2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethanol (8.46 g, 37.06 mmol), and thionyl chloride (68.99 g, 57.99 mmol) under a nitrogen atmosphere. The reaction mixture was heated to 80° C. to give a heterogeneous reaction mixture that was maintained at 80° C. for 2 hours at which time the starting material was completely consumed. The solution was cooled and quenched by the addition of water (400 mL). To the stirred solution was added solid sodium carbonate until the pH reached 10 at which time a solid precipitated out of solution. The solid was collected by filtration to afford 1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine (7.86 g, 31.86 mmol) as an off-white solid. The material was used without further purification.
Workup
- additionA round bottom flask was charged with a magnetic stir bar
- customto give a heterogeneous reaction mixture that
- temperaturewas maintained at 80° C. for 2 hours at which time the starting material
- customwas completely consumed
- temperatureThe solution was cooled
- customquenched by the addition of water (400 mL)
- additionTo the stirred solution was added solid sodium carbonate until the pH
- customprecipitated out of solution
- filtrationThe solid was collected by filtration
Sources & evidence
- ORD record
- ord-5f7c5a33f9dd4ef0befc19d36762245b
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664264B2
Linked notes
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